p-fluorobenzyl 3,5-dinitrobenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-fluorobenzyl 3,5-dinitrobenzoate
• 英文别名: (4-Fluorophenyl)methyl 3,5-dinitrobenzoate
• 化学式: C₁₄H₉FN₂O₆
• 分子量: 320.234
• InChiKey: AIYIMYQKWCGMSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对氟苯甲醇 、 3,5-二硝基苯甲酸 在 PhP(C₆H₄-p-(CH₂)2C₆F₁₃)2 、 bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)diazo dicarboxylate 作用下， 以 四氢呋喃 为溶剂， 生成 p-fluorobenzyl 3,5-dinitrobenzoate
  参考文献：
  名称：

  荧光Mitsunobu试剂和反应

  摘要：

  引入了完全氟的Mitsunobu反应程序。它既使用现有的[（C 6 F 13 CH 2 CH 2 C 6 H 4）2 PPh]，又使用新的[C 8 F 17 CH 2 CH 2 C 6 H 4 PPh 2 ]氟膦和新的氟偶氮二羧酸酯（C 6 ˚F 13 CH 2 CH 2 OC（O）NNCOOCH 2 CH 2 C ^ 6 ˚F 13）。该过程涉及在典型的Mitsunobu条件下在THF中与代表性的亲核试剂和醇进行平行反应，然后在氟硅石上进行快速固相萃取（spe），从而提供了具有优良收率的清洁产品。可以容易地分离出包含氧化的氧化膦和还原的酰肼的氟级分，并且可以通过适当的氧化还原反应以高收率再生起始试剂，以供再利用。

  DOI：

  10.1016/s0040-4020(02)00205-3

文献信息

• Fluorous Mitsunobu reagents and reactions
  作者：Sivaraman Dandapani、Dennis P. Curran

  DOI：10.1016/s0040-4020(02)00205-3

  日期：2002.5

  A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [(C6F13CH2CH2C6H4)2PPh] and new [C8F17CH2CH2C6H4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC(O)NNCOOCH2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction

  引入了完全氟的Mitsunobu反应程序。它既使用现有的[（C 6 F 13 CH 2 CH 2 C 6 H 4）2 PPh]，又使用新的[C 8 F 17 CH 2 CH 2 C 6 H 4 PPh 2 ]氟膦和新的氟偶氮二羧酸酯（C 6 ˚F 13 CH 2 CH 2 OC（O）NNCOOCH 2 CH 2 C ^ 6 ˚F 13）。该过程涉及在典型的Mitsunobu条件下在THF中与代表性的亲核试剂和醇进行平行反应，然后在氟硅石上进行快速固相萃取（spe），从而提供了具有优良收率的清洁产品。可以容易地分离出包含氧化的氧化膦和还原的酰肼的氟级分，并且可以通过适当的氧化还原反应以高收率再生起始试剂，以供再利用。
• FLUOROUS NUCLEOPHILIC SUBSTITUTION OF ALCOHOLS AND REAGENTS FOR USE THEREIN
  申请人：UNIVERSITY OF PITTSBURGH

  公开号：EP1419126A1

  公开（公告）日：2004-05-19
• US6806357B1
  申请人：——

  公开号：US6806357B1

  公开（公告）日：2004-10-19
• [EN] FLUOROUS NUCLEOPHILIC SUBSTITUTION OF ALCOHOLS AND REAGENTS FOR USE THEREIN<br/>[FR] SUBSTITUTION NUCLEOPHILE FLUOREE D'ALCOOLS ET REACTIFS UTILISES
  申请人：UNIV PITTSBURGH

  公开号：WO2003016246A1

  公开（公告）日：2003-02-27

  A method of effecting a nucleophilic substitution of an alcohol to produce a target product includes the steps of: reacting the alcohol and a nucleophile with an azodicarboxylate and a phosphine. At least one of the azodicarboxylate and the phosphine includes at least one fluorous tag. In several embodiments, the azodicarboxylate includes at least one fluorous tag, and the phosphine includes at least one fluorous tag. A compound has the formula: In the above formula n1, n2, n3, n4, n5, n6, n7, n8, n9 and n10 are independently 1 or =. X1, X2, X3, X?4, X5, X6, X7, X8, X9, X10, X11, X12, X13, X14, X15, X16, X17, X18, X19 and X20¿ are independently H, F, C1,an alkyl group, an aryl group or an alkoxy group. R?1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15 and R16¿ are independently H, F, C1, an alkyl group, an alkoxy group, a thioalkyl group, a dialkylamino group, a nitro group, a fluorinated amine group, O-Rf?1, S-Rf2¿, or N(Rf3)(R22), Wherein R22 is an alkyl group or Rf4, and wherein Rf?1, Rf2, Rf3¿ and Rf4 are independently a fluorous group selected from the group of a perfluoroalkyl group, a hydrofluoroalkyl group, a fluorinated ether group or a fluorinated amine group. At least one of R?1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15 or R16¿ is O-Rf?1, -N(Rf3)(R22¿), a perfluoroalkyl group, a hydrofluoroalkyl group, a fluorinated ether group or a fluorinated amine group.
• Separation tagging with cyclodextrin-binding groups: Mitsunobu reactions with bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD) and bis-(1-adamantylmethyl) azodicarboxylate (BadMAD)
  作者：Sivaraman Dandapani、Jeffery J. Newsome、Dennis P. Curran

  DOI：10.1016/j.tetlet.2004.07.009

  日期：2004.8

  context of the Mitsunobu reaction with adamantyl tags. HPLC experiments showed that molecules containing adamantyl groups were especially well retained on Sumichiral OA7500 β-methylated cyclodextrin bonded silica columns relative to many other types of molecules. Two new Mitsunobu reagents, bis-(1-adamantylmethyl) azodicarboxylate (BadMAD) and bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD), were prepared

  引入了一种新的分离带有环糊精结合基团的标签的方法，并在具有金刚烷基标签的Mitsunobu反应的背景下进行了举例说明。HPLC实验表明，相对于许多其他类型的分子，含有金刚烷基的分子在Sumichiral OA7500β-甲基化的环糊精键合硅胶柱上的保留特别好。制备了两种新的Mitsunobu试剂，双（1-金刚烷基甲基）偶氮二羧酸酯（BadMAD）和双（2-（1-金刚烷基）乙基）偶氮二羧酸酯（BadEAD），用于典型的Mitsunobu反应，并与β-甲基化的环糊精分离键合二氧化硅和标准二氧化硅。